A formal asymmetric synthesis of apratoxin D via advanced-stage asymmetric ACC alpha,alpha-bisalkylation of a chiral nonracemic ketone

作者：Dey Sumit; Wengryniuk Sarah E; Tarsis Emily M; Robertson Bradley D; Zhou Guoqiang; Coltart Don M^*

来源：Tetrahedron Letters, 2015, 56(22): 2927-2929.

DOI：10.1016/j.tetlet.2015.04.022

• ACC ketone alpha,alpha-bisalkylation
• Asymmetric synthesis
• Apratoxin D
• Lung cancer cell growth inhibitor

A formal asymmetric synthesis of the marine natural product apratoxin D, a highly potent inhibitor of H-460 human lung cancer cell growth (IC50 value of 2.6 nM), is described. The key feature of the synthesis is an advanced-stage asymmetric ACC alpha,alpha-bisalkylation of a chiral nonracemic methyl ketone to provide access to an advanced intermediate as a single diastereomer that has previously been advanced to apratoxin D.

• 出版日期2015-5-27